612-61-3Relevant articles and documents
Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents
Baxendale, Ian R.,Clososki, Giuliano C.,Costa-Lotufo, Leticia V.,Dos Santos, Thiago,Furtado, Luciana C.,Gambacorta, Guido,Moraes De Oliveira, Anderson,Murie, Valter E.,Nicolino, Paula V.,Nishimura, Rodolfo H. V.,Perovani, Icaro S.,Vessecchi, Ricardo
supporting information, p. 13402 - 13419 (2021/10/12)
We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some of the synthesized 4-carbinol quinolines have shown interesting antiproliferative properties, their hydroxyl group being a suitable amino group bioisostere. We also report a two-step approach for optically active derivatives.
The synthesis of N-heterocycles via copper/TEMPO catalysed aerobic oxidation of amino alcohols
Flanagan, James C. A.,Dornan, Laura M.,McLaughlin, Mark G.,McCreanor, Niall G.,Cook, Matthew J.,Muldoon, Mark J.
, p. 1281 - 1283 (2012/06/04)
N-Heterocycles can be prepared using alcohol oxidation as a key synthetic step. Herein we report studies exploring the potential of Cu/TEMPO as an aerobic oxidation catalyst for the synthesis of substituted indoles and quinolines.
Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis
Chelucci, Giorgio
scheme or table, p. 1562 - 1565 (2010/06/14)
A protocol for the hydrodehalogenation of halogenated pyridines and quinolines by the sodium borohydride/N,N,N′,N′-tetramethylethylenediamine (NaBH4-TMEDA) system under palladium catalysts is reported. Catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II) in combination with NaBH4-TMEDA rapidly hydrodehalogenate chloro(bromo)-pyridines and -quinolines at room temperature in quantitative yields. Chemoselective reduction of 4,7-dichloroquinoline affords 7-chloroquinoline as the sole product in almost quantitative yield. Moreover, palladium(II) acetate-triphenylphosphine and NaBH4-TMEDA are able to reduce efficiently reactive bromo-pyridines and -quinolines.
